Potassium Carbonate → HCID 13786529, compound

HRID 1655336Notes

Reaction equation

HRID 1655336 reaction equation
[CH3:1][CH:2]([CH3:17])[CH2:3][CH2:4][CH:5]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:8][C:7](=[O:16])[NH:6]1.NC(CCC(C)C)C(C1C=CC=CC=1)O.Cl.Cl[CH2:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH3:1][CH:2]([CH3:17])[CH2:3][CH2:4][CH:5]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[O:8][C:7](=[O:16])[N:6]1[CH2:35][CH2:36][CH2:37][N:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 13671865HCID 13671865, compoundHCID 67854302HCID 67854302, compound

Product 1

HCID 13786529HCID 13786529, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of (4RS, 5SR)-4-(3-methylbutyl)-5-phenyl-1,3-oxazolidin-2-one [mp: 111°-112 ° C.; prepared from (1RS,2SR)-2-amino-5-methyl-1-phenylhexan-1-ol by a known method {M. E. Dyen and D. Swern: Chem. Rev., 67, 197(1967)}] (1.17 g, 5 mmol), 1-(3-chloropropyl)piperidine hydrochloride (1.49 g, 7.5 mmol), anhydrous potassium carbonate powder (2.07 g, 15 mmol) in methyl ethyl ketone (15 ml) was refluxed with stirring for 24 hours. After cooling, insoluble material was removed by filtration and washed with methyl ethyl ketone. The washing and filtrate were combined together and concentrated under reduced pressure The residue was purified by silica gel column chromatography (silica gel:35 g ; eluent: chloroform/methanol) to obtain 1.52 g of the title compound as an oil (yield : 85%).

Workup

  1. temperatureAfter cooling
  2. custominsoluble material was removed by filtration
  3. washwashed with methyl ethyl ketone
  4. concentrationconcentrated under reduced pressure The residue
  5. customwas purified by silica gel column chromatography (silica gel:35 g ; eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-b6af6757c898450298c607cf3fa8a1cc
Source dataset
uspto-grants-1993_10
Patent number
US05250546

Reaction notes

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